Holiday rentals in Charleston

Brickway Retreat

Newly Remodeled 2 Bed, 1.5 Bath home in quiet neighborhood. This modernized house features a large fully furnished kitchen that is open to the dining area. The large living room with 10 ft ceilings has a pull-out sofa. Big screen TVs equipped with Roku streaming service in the master bedroom and living room. Wi Fi throughout the house is included. Enjoy your mornings on the cozy front porch featuring cedar pillars and stamped concrete and enjoy your evenings on the back patio around the fire pit

New! Jade's Place-Near I-57, Emerald Acres & EIU!

Welcome to Jade's Place managed by Jesse! This cozy 5-bedroom 3-bath retreat is centrally located in the heart of Mattoon, just moments away from restaurants, shops, and Emerald Acres! Enjoy a fully equipped kitchen, spacious living area, and a private patio perfect for relaxing. Amenities include free Wi-Fi, Roku TV's in all bedrooms/living, and plenty of parking for multiple families or work crews. Whether you're here for business or pleasure, Jade's Place is the perfect home away from home!

The Shoe Inn, a modern apt in downtown Teutopolis

Welcome to The Shoe Inn! You'll be at the center of town within walking distance to all the places you need to be: banquet halls, five bars, restaurants, Wessel's grocery store, ice cream shop, church, hardware store, and community parks. Smart lock, contactless entry is available for a convenient & safe stay. Enjoy the full size washer & dryer (no detergent provided) , fireplace, kitchenette (no stove), free parking, Samsung 50" smart TV w/ 100's of cable channels, Alexa device, & free WiFi

3-Acre Country Escape | Wildlife | Total Serenity

A freshly updated cottage, nestled in the country of Sullivan, just minutes from boating, camping, golf, theatre style shows, Amish country, and more. If you are looking for peaceful nights, this place is for you! Surrounded by mature trees and nature, where many days you will catch deer roaming the yard. Plenty of yard space for games, a fire table to converse around, and chairs on the porch to sit back, relax, and take in the tranquil sounds that surround you here at Lakewood Cottage #1.

Skylight Loft in Downtown Charleston - Near EIU

Welcome to Lady Bird Loft, previously known as loft @ courthouse square. This cozy 2-bedroom loft-style apartment is nestled in the heart of downtown Charleston, IL. With a historic view of the courthouse and square, this bright and airy space offers the perfect blend of comfort, character and convenience. Whether you're enjoying a weekend getaway, a visit to EIU, or just exploring the local charm, you'll love being steps away from popular local restaurants, cafés and unique shops.

Sweet Dreams Cabin. Peaceful & Relaxing

Get some quality family time at this newly remodeled cabin near the beautiful Embarrass river. You are surrounded by beautiful woods and a small creek. Lush wildlife is all around you so you can be one with nature. The cabin has all the luxury's to allow for a long term stay as well. Beautiful Lake Charleston is not far away. The large circle drive offers plenty of parking for your boat and guest. The large deck on the rear gives a beautiful view to be enjoyed by all.

MAC’s Place - Unique designer’s home

Located in the heart of the Illinois countryside in Charleston, our home is situated halfway between O'Brien Field (EIU) and the historic downtown square. This gorgeous designer's home and owner's suite was built in 1968 and offers a truly unique getaway. Our spacious home includes a 2-story stone wall, oversized windows, spiral staircase, game hall, billiard room, 100% cedar walk-in closet, sunken tub/shower in master and decorative antique cast iron fireplace.

On Harmony Lane...Cozy Loft apt in the Country

Our loft is the perfect place to rejuvenate in a country setting. From cozy bed sheets, TVs, and Wi Fi inside, to a firepit, grill, and hammock chairs outdoors, we make your stay comfortable. We are minutes from Eastern Illinois University. So enjoy...go antiquing, visit a winery, or delve into Lincoln's history. Visit a nearby Amish town. Go kayaking, fishing or enjoy a hiking on a nearby trail or one of ours.

Simply Savvy

Charming 1 bed, 1 bath home with everything you need for a relaxing stay. Enjoy a full kitchen, in-house laundry, cozy living room, and a spacious bedroom with en-suite bath. The inviting front porch is perfect for morning coffee or evening sunsets. Located on a large lot near downtown with plenty of parking and fun nearby activities. Ideal for both weekend getaways and extended stays.

One bedroom apartment above garage

One bedroom apartment above a garage in a small, quiet town. There is not much to do in our town but it has a wonderful park, a gas station, bank, and a family friendly bar that serves pizza and a few other items. We are located 20 minutes from Shelbyville, Effingham, and Mattoon. 20 % off per night for stays longer than 7 nights.

Tiny with all the basics

One-Bedroom with Private Entrance Unwind in this compact one-bedroom upstairs duplex. Enjoy the comfort of a queen bed, a twin size futon for extra guest, and a fully equipped kitchen for all your cooking needs. "Perfect for a quick rest or an extended stay, this apartment is ideal for travelers looking to relax and recharge.

Pine Lodge

Your family will be close to everything when you stay at this centrally-located place, which is close to the 70 Interstate, off the 130 and 40 crossroads. Cumberland Street goes downtown Greenup where you will find restaurants, bars, library, museums, grocery store, parks, and laundry mat.